Dear SaaStr: What 3 Mistakes Did You Make in Your SaaS That You Wish You Could Go Back in Time and Fix, to Accelerate Growth?

Every year that I think about it, the top 3 sort of change.

But my Top 3 mistakes I made as a SaaS CEO:

  • Not constantly hiring, especially for VPs. You need to spend 20% of your time doing this. I hunkered down too much, tried to do too much myself, and let key roles stay vacant for too long.  I’m still making that mistake to that day.  The best CEOs are constantly recruiting.  Forever.
  • Not “forcing” the team to be more enterprise. I’m not much of a micromanager, but we blew a few key enterprise opportunities because the engineering team didn’t want to do certain things in the enterprise playbook. I should have micromanaged a few key opportunities that were “make or break”, or close to it.  I needed to be more hands-on in a few critical deals when the team needed to be … pushed more.
  • Not understanding the playbook, especially after $4m-$5m ARR or so. Not understanding when you become unstoppable. Maybe not finding good enough mentors. This is why I started SaaStr, but in any event, I didn’t understand that SaaS companies that reach $8m+ in ARR, growing 80% or more with net negative churn are basically unstoppable. Now I know 🙂

A bit more here: From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming. | SaaStr

From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming.

 

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